The reason is that in compat.py (https://github.com/dahlia/wand/blob/master/wand/compat.py#L44) we are currently doing a simple return string.encode(). If called without arguments, encode uses the current default string encoding which is ASCII in case of Python 2. Obviously, ASCII cannot encode my greek character there and the UnicodeEncodeError is thrown.

We cannot and dont want to change the fact that ASCII is Python 2's default encoding. Relevant discussion about this topic can be found here:

So the solution would be to make a well-grounded decision about which encoding to use. I tried UTF-8 and it worked for me (I changed line 44 of compat.py accordingly). I am not entirely sure why this works, for this I do not understand enough of which data format the imagemagick binaries do expect.

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Just my thoughts, you may of course do something else :-): then Wand maybe should not directly expose DrawSetTextEncoding, but rather use it internally and set it to UTF-8 (IM's docks say The only character encoding which may be specified at this time is "UTF-8"). Wand could require people to use unicode objects in Python code, which would then (internally, again) become encoded as UTF-8 before passing to ImageMagick.